GB944838A - Improvements in or relating to colour couplers and to their production and use in colour photography - Google Patents
Improvements in or relating to colour couplers and to their production and use in colour photographyInfo
- Publication number
- GB944838A GB944838A GB43668/59A GB4366859A GB944838A GB 944838 A GB944838 A GB 944838A GB 43668/59 A GB43668/59 A GB 43668/59A GB 4366859 A GB4366859 A GB 4366859A GB 944838 A GB944838 A GB 944838A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- reacted
- compound
- chloride
- colour
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 4-dodecylphenyl Chemical group 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 3
- KLPPPIIIEMUEGP-UHFFFAOYSA-N 4-dodecylaniline Chemical compound CCCCCCCCCCCCC1=CC=C(N)C=C1 KLPPPIIIEMUEGP-UHFFFAOYSA-N 0.000 abstract 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 abstract 1
- LYANEXCVXFZQFF-UHFFFAOYSA-N 2-(2,5-dioxooxolan-3-yl)acetic acid Chemical compound OC(=O)CC1CC(=O)OC1=O LYANEXCVXFZQFF-UHFFFAOYSA-N 0.000 abstract 1
- ZQBWYXZRSMMISZ-UHFFFAOYSA-N 2-(2,5-dioxopyrrolidin-1-yl)acetic acid Chemical compound OC(=O)CN1C(=O)CCC1=O ZQBWYXZRSMMISZ-UHFFFAOYSA-N 0.000 abstract 1
- UWMVKAKBYCBBQT-UHFFFAOYSA-N 2-(2,5-dioxopyrrolidin-1-yl)sulfanylacetic acid Chemical compound OC(=O)CSN1C(=O)CCC1=O UWMVKAKBYCBBQT-UHFFFAOYSA-N 0.000 abstract 1
- JPHVSDWIWBDHOC-UHFFFAOYSA-N 2-(carboxymethylsulfanyl)butanedioic acid Chemical compound OC(=O)CSC(C(O)=O)CC(O)=O JPHVSDWIWBDHOC-UHFFFAOYSA-N 0.000 abstract 1
- OYCDKUFRIYCQIJ-UHFFFAOYSA-N 2-octadecyl-1,3-dioxoisoindole-5-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(=O)N(CCCCCCCCCCCCCCCCCC)C(=O)C2=C1 OYCDKUFRIYCQIJ-UHFFFAOYSA-N 0.000 abstract 1
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 abstract 1
- QCYIJQGZKWHKFY-UHFFFAOYSA-N 5-isocyanato-2-octadecylisoindole-1,3-dione Chemical compound N(=C=O)C=1C=C2C(C(=O)N(C2=O)CCCCCCCCCCCCCCCCCC)=CC1 QCYIJQGZKWHKFY-UHFFFAOYSA-N 0.000 abstract 1
- MMVIDXVHQANYAE-UHFFFAOYSA-N 5-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=C2C(=O)OC(=O)C2=C1 MMVIDXVHQANYAE-UHFFFAOYSA-N 0.000 abstract 1
- BVMSISZCOPWJKY-UHFFFAOYSA-N 5-nitro-2-octadecylisoindole-1,3-dione Chemical compound [N+](=O)([O-])C=1C=C2C(C(=O)N(C2=O)CCCCCCCCCCCCCCCCCC)=CC1 BVMSISZCOPWJKY-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000003931 anilides Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 150000003949 imides Chemical group 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 150000004060 quinone imines Chemical class 0.000 abstract 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 abstract 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/416—2,5-Pyrrolidine-diones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/32—Colour coupling substances
- G03C7/3212—Couplers characterised by a group not in coupling site, e.g. ballast group, as far as the coupling rest is not specific
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/07—Organic amine, amide, or n-base containing
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Indole Compounds (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Abstract
The invention comprises compounds of the general formula: <FORM:0944838/C2/1> wherein A is a trivalent radical derived from 1,2-phenylene, 2,3-naphthylene or di- or trimethylene, B is a colour coupler residue, Y is -CO-, -CONH-, -COCH2- or -COCH2S- and R is a hydrocarbon group which may be substituted. The residue B is such that BNH2 will react with the oxidation products of N,N-diethyl-p-phenylenediamine, formed during the development of a silver salt image with that compound, to yield a quinoneimine or azamethine dyestuff. Such compounds are prepared by reacting with BNH2 a compound of formula Z-A(CO)2N-R wherein Z is -COX, -CH2COX, -NCO, -NHCOOC6H5 or -SCH2COX and X is halogen. In examples, R is a 4, 6, 8, 10, 12, 14, 16 or 18C alkyl group, or 4-dodecylphenyl, benzyl or cyclohexyl and B is 5-keto-1-phenylpyrazol-3-yl, 4 - (4 - methoxybenzoylacetamido) - 3 - methoxyphenyl, b -(1-hydroxy-2-naphthamido) ethyl, 4-cyanoacetylphenyl or 4-(3, 5-dimethoxycarbonylphenyl) carbamylacetylphenyl. Starting materials. (1) Trimellitic anhydride reacted with octadecylamine to give 4-carboxy-N-octadecylphthalimide which gave the 4-chlorocarbonyl compound with thionyl chloride. Other N-alkyl-4-chlorocarbonyl-phthalimides were similarly obtained. (2) Octadecylamine reacted with 4-nitrophthalic anhydride to give 4-nitro-N-octadecylphthalimide which was reduced with Raney Ni to the 4-amino compound; reaction of the latter with phosgene gave 4-isocyanato-N-octadecylphthalimide. (3) Tricarballylic anhydride (from the acid and acetyl chloride) reacted with 4-dodecylaniline giving N(4-dodecylphenyl) succinimidoacetic acid from which the acid chloride was obtained using thionyl chloride; N-octadecylsuccinimidoacetic acid was similarly obtained. (4) Carboxymethylmercaptosuccinic acid reacted with 4-dodecylaniline giving N(4-dodecylphenyl) succinimidomercaptoacetic acid which afforded the acid chloride with thionyl chloride. The compounds are used as colour couplers (see Division G2) either directly or in dilute alkali, in which case the imide ring is opened. Specific alkaline hydrolysis products isolated-(Examples 26 and 27) are 41-methoxybenzoylacet-2-methoxy-5 (3- or 4-cyclohexylaminocarbonyl-4-or 3-carboxybenzoylamino) anilide and its analogue in which benzyl replaces cyclohexyl.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL259369D NL259369A (en) | 1959-12-23 | ||
| GB43668/59A GB944838A (en) | 1959-12-23 | 1959-12-23 | Improvements in or relating to colour couplers and to their production and use in colour photography |
| US75081A US3161512A (en) | 1959-12-23 | 1960-12-12 | Colour couplers and their production and use in colour photography |
| DE19601445078 DE1445078A1 (en) | 1959-12-23 | 1960-12-23 | Process for the preparation of color coupler compounds for color photography |
| FR847887A FR1276582A (en) | 1959-12-23 | 1960-12-23 | Improvements in color photography |
| US336369A US3236861A (en) | 1959-12-23 | 1964-01-08 | Organic imido compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB43668/59A GB944838A (en) | 1959-12-23 | 1959-12-23 | Improvements in or relating to colour couplers and to their production and use in colour photography |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB944838A true GB944838A (en) | 1963-12-18 |
Family
ID=10429779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB43668/59A Expired GB944838A (en) | 1959-12-23 | 1959-12-23 | Improvements in or relating to colour couplers and to their production and use in colour photography |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US3161512A (en) |
| DE (1) | DE1445078A1 (en) |
| GB (1) | GB944838A (en) |
| NL (1) | NL259369A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0782044A1 (en) * | 1995-12-27 | 1997-07-02 | Konica Corporation | Silver halide light-sensitive color photographic material |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL268720A (en) * | 1960-08-29 | |||
| DE1272718B (en) * | 1963-10-08 | 1968-07-11 | Gevaert Photo Prod Nv | Process for producing a purple photographic image |
| NL133250C (en) * | 1964-02-20 | |||
| DE2447175A1 (en) * | 1974-10-03 | 1976-04-15 | Agfa Gevaert Ag | LIGHT SENSITIVE MATERIAL WITH EMULSIFIED SUBSTANCES |
| JP5934658B2 (en) * | 2013-01-29 | 2016-06-15 | Ｊｘエネルギー株式会社 | IMIDE-UREA COMPOUND AND PROCESS FOR PRODUCING THE SAME, GREASE THINNER, AND GREASE COMPOSITION |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE435374A (en) * | 1938-07-14 | |||
| US2313498A (en) * | 1940-01-02 | 1943-03-09 | Eastman Kodak Co | Cyanoacetyl coupler |
| US2452315A (en) * | 1945-04-09 | 1948-10-26 | American Maize Prod Co | Plasticized prolamine-base protein compositions |
| US2628964A (en) * | 1951-04-07 | 1953-02-17 | American Cyanamid Co | Preparation of naphthostyrils |
| US2663714A (en) * | 1951-09-24 | 1953-12-22 | Lilly Co Eli | Hydrogenated benz [cd] indoles |
| BE516025A (en) * | 1951-12-05 | |||
| BE541727A (en) * | 1954-10-01 | |||
| US2857395A (en) * | 1955-04-09 | 1958-10-21 | Arnold Herbert | Derivatives of alpha-n-(beta-dialkylamino alkyl)-amino-phenyl acetic acid esters |
| BE552264A (en) * | 1955-11-01 | |||
| BE565656A (en) * | 1957-03-15 | |||
| US2920961A (en) * | 1957-07-29 | 1960-01-12 | Eastman Kodak Co | Couplers for color photography |
| US2897206A (en) * | 1958-06-24 | 1959-07-28 | Nippon Shinyaku Co Ltd | Dialkylamides of alpha-(4-antipyrylamino)-fatty acids and their n-alkyl derivatives |
| BE590403A (en) * | 1959-04-30 |
-
0
- NL NL259369D patent/NL259369A/xx unknown
-
1959
- 1959-12-23 GB GB43668/59A patent/GB944838A/en not_active Expired
-
1960
- 1960-12-12 US US75081A patent/US3161512A/en not_active Expired - Lifetime
- 1960-12-23 DE DE19601445078 patent/DE1445078A1/en active Pending
-
1964
- 1964-01-08 US US336369A patent/US3236861A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0782044A1 (en) * | 1995-12-27 | 1997-07-02 | Konica Corporation | Silver halide light-sensitive color photographic material |
| US5981157A (en) * | 1995-12-27 | 1999-11-09 | Konica Corporation | Silver halide light-sensitive color photographic material |
Also Published As
| Publication number | Publication date |
|---|---|
| US3236861A (en) | 1966-02-22 |
| US3161512A (en) | 1964-12-15 |
| DE1445078A1 (en) | 1968-10-24 |
| NL259369A (en) |
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